Ammonia → 5-Methoxy-2-nitrobenzamide
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N+:12]([O-:14])=[O:13])=[C:7]([CH:11]=1)[C:8](O)=[O:9].C[N:16](C=O)C.C(Cl)(=O)C(Cl)=O.N>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N+:12]([O-:14])=[O:13])=[C:7]([CH:11]=1)[C:8]([NH2:16])=[O:9]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 5-methoxy-2-nitrobenzoic acid (18.0 g, 91.3 mmol) and DMF (0.1 mL) in THF (150 mL) was added dropwise oxalyl chloride (12.7 g, 100 mmol) under ice-cooling, and the mixture was stirred at 0° C. for 1 hr, and then at room temperature for 3 hr. This solution was added dropwise to aqueous ammonia (7% aqueous solution, 200 mL) under ice-cooling. The reaction solution was concentrated under reduced pressure to evaporated THF, and the precipitated insoluble material was collected by filtration. The filtered cake was washed with water to give 5-methoxy-2-nitrobenzamide as a pale-yellow powder (10.0 g, 56%).
Workup
- temperaturecooling
- waitat room temperature for 3 hr
- temperaturecooling
- concentrationThe reaction solution was concentrated under reduced pressure
- customto evaporated THF
- filtrationthe precipitated insoluble material was collected by filtration
- washThe filtered cake was washed with water
Sources & evidence
- ORD record
- ord-62a7b5b319494d53950f37f6c6b34d1b
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07915267B2
Reaction notes
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